Pesticide thiazolyloxy substituted phenylamidine derivatives

ABSTRACT

The present invention relates to aryloxy substituted phenylamidine derivatives of formula (I) wherein the substituents are as in the description, their process of preparation, their use as fungicide or insecticide active agents, particularly in the form of fungicide or insecticide compositions, and methods for the control of phytopathogenic fungi or damaging insects, notably of plants, using these compounds or compositions (I).

CROSS REFERENCE TO RELATED APPLICATIONS

This is a §371 National Stage Application of International ApplicationNo. PCT/EP2006/066273 filed Sep. 12, 2006, which claims priority fromEuropean Application No. 05356155.1 filed Sep. 13, 2005.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to aryloxy substituted phenylamidinederivatives, their process of preparation, their use as fungicide orinsecticide active agents, particularly in the form of fungicide orinsecticide compositions, and methods for the control of phytopathogenicfungi or damaging insects, notably of plants, using these compounds orcompositions.

In international patent application WO-00/46184 certain phenyl-amidinederivatives are disclosed. However, this document does not specificallydisclose nor suggest to select such compounds wherein the phenyl ring issubstituted according to the invention thus allowing an unexpected andsignificantly higher fungicide activity.

2. Description of Related Art

It is always of high-interest in agriculture to use novel pesticidecompounds in order to avoid or to control the development of resistantstrains to the active ingredients. It is also of high-interest to usenovel compounds being more active than those already known, with the aimof decreasing the amounts of active compound to be used, whilst at thesame time maintaining an effectiveness at least equivalent to thealready known compounds.

In the same way, it is also always of high-interest to use novelinsecticide, nematocide or acaricide agents to control damaging insectsor other damaging organisms.

SUMMARY OF THE INVENTION

We have now found a new family of compounds which possess the abovementioned effects or advantages.

Accordingly, the present invention provides amidine derivatives offormula (I):

wherein

-   -   R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl,        a substituted or non substituted C₂-C₁₂-alkenyl, a substituted        or non substituted C₂-C₁₂-alkynyl, SH or a substituted or non        substituted S—C₁-C₁₂-alkyl;    -   R² represents a substituted or non substituted C₁-C₁₂-alkyl;    -   R³ represents a substituted or non substituted C₂-C₁₂-alkyl,        substituted or non substituted C₃-C₆-cycloalkyl, substituted or        non substituted C₂-C₁₂-alkenyl, substituted or non substituted        C₂-C₁₂-alkynyl, halogeno-C₁-C₁₂-alkyl; or    -   R¹ and R², R¹ and R³ or R² and R³ can form together a        substituted or non substituted 5- to 7-membered heterocycle;    -   R⁴ represents a substituted or non substituted C₁-C₁₂-alkyl, a        halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non        substituted O—C₁-C₁₂-alkyl or cyano;    -   R⁵ represents H, a substituted or non substituted C₁-C₁₂-alkyl,        a halogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non        substituted O—C₁-C₁₂-alkyl or cyano;    -   R⁶ represents a heterocycle selected in the list consisting of

-   -   R⁷ represents H, halogen, nitro, cyano; substituted or non        substituted phenyl, substituted or non substituted benzyl;        C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,        C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;        C₁-C₈—S(O)_(m)R¹¹; C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴;        —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴;    -   R⁸ represents H, halogen, cyano; substituted or non substituted        phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,        C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,        C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;        C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴;    -   R⁷ and R⁸ can form a carbocycle, which can be saturated,        unsaturated or aromatic and substituted or non substituted by        halogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl    -   R⁹ represents H, halogen, cyano; substituted or non substituted        phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,        C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl,        C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio;        C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴;    -   R¹⁰ represents H, halogen, cyano; substituted or non substituted        phenyl, substituted or non substituted benzyl, substituted or        non substituted pyridyl; C₁-C₈-alkyl, C₁-C₈-alkoxy,        C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy or        C₁-C₆-halogen-alkylthio; C₁-C₈-alkyl-S(O)_(m)R¹¹;        C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶,        S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴:    -   m represents 0, 1 or 2;    -   R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl;    -   R¹² represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl    -   R¹³ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl;    -   R¹⁴ represents H, substituted or non substituted, branched or        linear C₁-C₈-alkyl, C₁-C₈-alkoxy;    -   R¹⁵ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl;    -   R¹⁶ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₈-alkoxy,        substituted or non substituted benzyl;    -   R¹² and R¹³ can form a 5- or 6-membered heterocycle, which can        further comprise one or more heteroatoms selected in the list        consisting of O, N, S;    -   R¹⁵ and R¹⁶ can form a heterocyclic 5- or 6-membered ring,        including further heteroatoms, like O, S, N;        as well as salts, N-oxides, metallic complexes, metalloidic        complexes and optically active or geometric isomers thereof.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Any of the compounds according to the invention can exist in one or moreoptical, geometric or chiral isomer forms depending on the number ofasymmetric centres in the compound. The invention thus relates equallyto all the optical isomers and to their racemic or scalemic mixtures(the term “scalemic” denotes a mixture of enantiomers in differentproportions), and to the mixtures of all the possible stereoisomers, inall proportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds according to the invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

For the compounds according to the invention, halogen means either oneof fluorine, bromine, chlorine or iodine and heteroatom can be nitrogen,oxygen or sulphur.

Preferred compounds of formula (I) according to the invention are thosewherein R¹ represents H; C₁-C₁₂-alkyl, preferably C₁-C₁₂-alkyl likemethyl; or SH.

Other preferred compounds of formula (I) according to the invention arethose wherein R² represents methyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R³ represents C₂-C₁₂-alkyl, preferably a nonsubstituted C₂-C₄-alkyl like ethyl, n-propyl, i-propyl; C₂-C₁₂-alkenyl,preferably C₃-C₄-alkenyl like propenyl or allyl; C₃-C₆-cycloalkyl likecyclopropyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R² and R³ can form together a substituted ornon substituted 5- to 7-membered heterocycle, preferably a 6-memberedheterocycle, more preferably a piperidinyl or a pyrrolidinyl, even morepreferably a 2-alkylated-pyrrolidinyl like a 2-methyl-pyrrolidinyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁴ represents a C₁-C₁₂-alkyl, preferably anon substituted C₁-C₁₂-alkyl like methyl and ethyl; a halogen atom likea fluorine and a chlorine atom; trifluoromethyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁵ represents H, C₁-C₁₂-alkyl, preferably anon substituted C₁-C₁₂-alkyl like methyl and ethyl; a halogen atom likea fluorine and a chlorine atom; trifluoromethyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁷ represents H, Cl, Br, I, nitro, cyano;phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl;benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy orC₁-C₄-halogenalkylthio; C₁-C₄-alkyl-S(O)_(m)R¹¹; C₁-C₄-alkyl-SO₂NR¹²R¹³;C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁸ represents H, Cl, Br, I, cyano; phenyl;phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio;C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁷ and R⁸ form a carbocycle, which can besaturated, unsaturated or aromatic and substituted or non substituted byhalogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R⁹ represents H, Cl, Br, I, cyano; phenyl;phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio;C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹⁰ represents H, Cl, Br, I, cyano; phenyl;phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; pyridyl; pyridyl substituted by F, Cl, Br, I,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy;C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenalkyl,C₁-C₄-halogen-alkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-S(O)_(m)R¹¹;C₁-C₄-alkyl-SO₂NR¹²R¹³; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹,SO₂NR¹²R¹³, COR¹⁴.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹¹ represents C₁-C₈-alkyl,C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹² represents H, C₁-C₈-alkyl,C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹³ represents H, C₁-C₈-alkyl,C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹⁴ represents H, branched or linearC₁-C₈-alkyl, C₁-C₈-alkoxy.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹⁵ represents H, C₁-C₈-alkyl,C₃-C₆-cycloalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹⁶ represents H, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, benzyl; benzyl substituted by halogen,C₁-C₄-alkyl or C₁-C₄-halogenoalkyl.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹² and R¹³ form a 5- or 6-memberedheterocycle, which can further comprise one or more heteroatoms selectedin the list consisting of O, N, S.

Still other preferred compounds of formula (I) according to theinvention are those wherein R¹⁵ and R¹⁶ can form a 5- or 6-memberedheterocycle comprising further heteroatoms, like O, S, N.

The above mentioned preferences with regard to the substituents of thecompounds according to the invention can be combined in various manners.These combinations of preferred features thus provide sub-classes ofcompounds according to the invention. Examples of such sub-classes ofpreferred compounds according to the invention can combine:

-   -   preferred features of R¹ with preferred features of R² to R⁶ or        to R¹⁶ where applicable;    -   preferred features of R² with preferred features of R¹ to R⁶ or        to R¹⁶ where applicable;    -   preferred features of R³ with preferred features of R¹ to R⁶ or        to R¹⁶ where applicable;    -   preferred features of R⁴ with preferred features of R¹ to R⁶ or        to R¹⁶ where applicable;    -   preferred features of R⁵ with preferred features of R¹ to R⁶ or        to R¹⁶ where applicable.

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of m, n andR¹ to R¹¹ so as to form most preferred subclasses of compounds accordingto the invention.

The present invention also relates to a process for the preparation of acompound of formula (I). Generally, the preparation of compound offormula (I) according to the invention can be carried out as illustratedby scheme 1 and scheme 1a.

In schemes 1 and 1a, formula (IV)

wherein

-   -   Y represents C—R⁸ (see formula (IVa)), C—R¹⁰ (see formula        (IVc)), or N (see formula (IVb)),    -   Z represents C—R⁷ (see formula (IVa)), C—R⁹ (see formula (IVb)),        or N (see formula (IVc)).    -   R⁷, R⁸, R⁹ and R¹⁰ are as herein-defined,    -   X represents halogen, triflate, SOMe, mesylate or tosylate.

Thus according to a further aspect according to the invention, there isprovided a process (a) for the preparation of aniline derivatives offormulae (I) and (II) by reacting aminophenol derivatives of formula(III) or amidine derivatives of formula (IX)

wherein

-   -   R¹, R², R³, R⁴ and R⁵ are as herein-defined,        with thiazole derivatives or thiadiazole derivatives        (1,3,4-thiadiazoles or 1,3,5-thiadiazoles) of formula (IV) or        (IVa), (IVb) and (IVc), respectively,

wherein

-   -   Z, Y, R⁷, R⁸, R⁹ and R¹⁰ are as herein-defined    -   X represents halogen, triflate, SOMe, mesylate or tosylate.

Process (a) according to the invention can further comprise one or moreof the following characteristics:

-   -   presence of a base;    -   presence of an inert organic diluent;    -   presence of a catalyst.

Process (a) according to the invention is carried out using4-amino-2,5-dimethylphenol, 2,4,5-trichloro-1,3-thiazole and a base asstarting materials. Process (a) can be conducted according to scheme 2.

Formula (IV) or formulae (IVa), (IVb) and (IVc), respectively, providegeneral definitions for the thiazole derivatives and thiadizolederivatives useful as starting materials for carrying out process (a)according to the invention.

Formulae (III) and (IX) provide a general definition of the aminophenolderivatives or amidine derivatives useful as starting materials forcarrying out process (a) according to the invention. In this formula,R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, X, Y and Z preferably representsubstituents as herein-defined in connection with the description ofcompounds of formula (I) according to the invention.

Amidine derivatives of formula (I) and (IX) can be prepared by a furtherprocess according to the invention. Various alternatives of process (b)according to the invention can be considered, they are defined asprocess (b1), process (b2) and process (b3) according to the invention.Process (b) according to the invention comprises reacting anilinederivatives of formulae (II) and (III) with different reagents thusdefining processes (b1), (b2) and (3) respectively

wherein

-   -   R⁴, R⁶, Y and Z are as herein-defined.

Process (b1) is carried out further using amide derivatives of formula(VI)

wherein

-   -   R¹, R², R³ are as herein-defined.

Process (b1) according to the invention can further comprise one or moreof the following characteristics:

-   -   presence of a halogenation agent, like PCl₅, PCl₃, POCl₃, SOCl₂;    -   presence of a diluent.

Process (b1) according to the invention is carried out using4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline,piperidin-2-one and phosphoric trichloride as starting materials.Process (b1) can be conducted according to scheme 3.

Formula (II) provides a general definition of the biphenylaminederivatives useful as starting materials for carrying out process (b1)according to the invention. In this formula R¹, R², R³, R⁴, R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents as herein-definedin connection with the description of compounds of formula (I) accordingto the invention.

Process (b2) is carried out further using amino-acetal derivatives offormula (V)

wherein

-   -   R¹, R², R³ are as herein-defined;    -   B¹ and B² represent each alkyl or together cycloalkyl.

Process (b2) according to the invention can further comprise one or moreof the following characteristics:

-   -   presence of an acid or base;    -   presence of a diluent.

Process (b2) according to the invention is carried out using4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline andN-(dimethoxymethyl)-N-methylethanamine as starting materials. Process(b2) can be conducted according to scheme 4.

Process (b3) is carried out further using amine derivatives of formula(VII)

wherein

-   -   R² and R³ are as herein-defined;        in presence of orthoester derivatives of formula (VIII)

wherein

-   -   R¹ is as herein-defined;    -   B¹, B² and B³ represent each alkyl.

Formulae (II) and (III) provide general definitions of the aminederivatives useful as starting materials for carrying out process (b3)according to the invention. In this formulae, R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents asherein-defined in connection with the description of compounds offormula (I) according to the invention.

Process (b3) according to the invention is carried out using4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline,trimethyl-ortho-ester and N-methyl-ethanamine as starting materials andan acid.

Process (d3) can be conducted according to scheme 5.

Formulae (II) and (III) provide general definitions of the aminederivatives useful as starting materials for carrying out process (b3)according to the invention. In these formulae, R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, Y and Z preferably represent substituents asherein-defined in connection with the description of compounds offormula (I) according to the invention.

Processes (b), (b1), (b2) or (b3) according to the invention can furthercomprise one or more of the following characteristics:

-   -   presence of a acid or base;    -   presence of a diluent.

Amidine derivatives of formula (I) can be prepared by a further process(c) according to the invention by reacting amidine derivatives offormula (I)

wherein

-   -   Y or Z represent C≡COR₁₄ and R¹, R², R³, R⁴ and R⁵ are as        herein-defined with hydroxylamines or salts thereof,        respectively

wherein R¹⁶ is as herein-defined.

Process (c) according to the invention can further comprise one or moreof the following characteristics:

-   -   presence of an acid or a base;    -   presence of an inert organic diluent;    -   presence of a catalyst.

Process (c) according to the invention is carried out usingN′-{4-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamideand 3-(aminooxy)prop-1-ene hydrochloride as starting materials.

Process (c) can be conducted according to scheme 6.

Suitable diluents for carrying out process (a) according to theinvention are all customary inert organic solvents. Preference is givento using aliphatic, alicyclic or aromatic hydrocarbons, such aspetroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such aschlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbontetrachloride, dichloroethane or trichloroethane; ethers, such asdiethyl ether, diisopropyl ether, methyl tert-butyl ether, methyltert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitriles, such as acetonitrile,propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethyl-phosphoric triamide; mixtures thereofwith water or pure water.

Suitable diluents for carrying out processes (b1), (b2), (b3) and (c)according to the invention are in each case all customary inert organicsolvents. Preference is given to using aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; ethers, such asdiethyl ether, diisopropyl ether, methyl tert-butyl ether, methyltert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitriles, such as acetonitrile,propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate; sulphoxides, such asdimethylsulphoxide; or sulphones, such as sulpholane; alcohols, such asmethanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol,ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol,diethylene-glycolmonomethylether, diethyleneglycolmonoethylether;mixtures thereof with water or pure water.

Suitable acid binders for carrying out process (a) according to theinvention are all inorganic and organic bases customary for suchreactions. Preference is given to using alkaline earth metal or alkalimetal hydrides, hydroxides, amides, alcoholates, acetates, carbonates orhydrogen carbonates, such as sodium hydride, sodium amide, lithiiumdiisoproylamide, sodium methanolate, sodium ethanolate, potassiumtert-butanolate, sodium acetate, potassium acetate, calcium acetate,sodium hydroxide, potassium hydroxide, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate, or ammoniumcarbonate; and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethyl-benzylamine pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylamino-pyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or di-azabicycloundecene (DBU).

Suitable acids for carrying out process (b3) according to the inventionare all inorganic and organic acids customary for such reactions.Preference is given to using para-toluene sulfonic acid, methanesulfonic acid, hydrochloric acid (gas, aqueous or organic solution) orsulphuric acid.

Suitable condensing agents for carrying out process (b1) according tothe invention are all condensing agents customary for such amidationreactions. Preference is given to using acid halide former, such asphosgene, phosphorous tribromide, phosphorous trichloride, phosphorouspentachloride, phosphorous trichloride oxide or thionyl chloride;anhydride former, such as ethyl chloroformate, methyl chloroformate,isopropyl chloroformate, isobutyl chloroformate or methanesulfonylchloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) orother customary condensing agents, such as phosphorous pentoxide,polyphosphoric acid, N,N′-carbonyldiimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane orbromo-tripyrrolidino-phosphonium-hexafluorophosphate.

When carrying out processes (a), (b) and (c) according to the invention,the reaction temperature can be varied within a relatively wide range.In general, the process is carried out at temperatures between from 0°C. to 150° C., preferably from 0° C. to 120° C., particularly preferablyfrom 10° C. to 90° C.

Compounds of formula (I) according to the invention can be preparedaccording to the herein described processes. It will nevertheless beunderstood that, on the basis of his general knowledge and of availablepublications, the skilled worker will be able to adapt these processesaccording to the specifics of each of the compounds which it is desiredto synthesise.

In a further aspect, the present invention also relates to a fungicideor insecticide composition comprising an effective and non-phytotoxicamount of an active compound of formula (I). The expression “effectiveand non-phytotoxic amount” means an amount of composition according tothe invention which is sufficient to control or destroy the fungipresent or liable to appear on the crops, and which does not entail anyappreciable symptom of phytotoxicity for the said crops. Such an amountcan vary within a wide range depending on the fungus to be controlled,the type of crop, the climatic conditions and the compounds included inthe fungicide composition according to the invention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein-defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with which the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support may be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports may also beused.

The composition according to the invention may also comprise additionalcomponents. In particular, the composition may further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention may be made, for example, of polyacrylic acidsalts, lignosulphonic acid salts, phenolsulphonic ornaphthalenesulphonic acid salts, polycondensates of ethylene oxide withfatty alcohols or with fatty acids or with fatty amines, substitutedphenols (in particular alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols,fatty acid esters of polyols, and derivatives of the present compoundscontaining sulphate, sulphonate and phosphate functions. The presence ofat least one surfactant is generally essential when the active compoundand/or the inert support are water-insoluble and when the vector agentfor the application is water. Preferably, surfactant content may becomprised from 5% to 40% by weight of the composition.

Optionally, additional components may also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, bait (ready for use), bait concentrate, blockbait, capsule suspension, cold fogging concentrate, dustable powder,emulsifiable concentrate, emulsion oil in water, emulsion water in oil,encapsulated granule, fine granule, flowable concentrate for seedtreatment, gas (under pressure), gas generating product, grain bait,granular bait, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, plate bait, powder for dryseed treatment, scrap bait, seed coated with a pesticide, smoke candle,smoke cartridge, smoke generator, smoke pellet, smoke rodlet, smoketablet, smoke tin, soluble concentrate, soluble powder, solution forseed treatment, suspension concentrate (=flowable concentrate), trackingpowder, ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, vapour releasing product, water dispersible granules ortablets, water dispersible powder for slurry treatment, water solublegranules or tablets, water soluble powder for seed treatment andwettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before application to thecrop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have a broadened spectrum of activity.

The mixtures with other fungicide compounds are particularlyadvantageous. Examples of suitable fungicide mixing partners may beselected in the following lists:

-   -   B1) a compound capable to inhibit the nucleic acid synthesis        like benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,        dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl,        metalaxyl-M, ofurace, oxadixyl, oxolinic acid;    -   B2) a compound capable to inhibit the mitosis and cell division        like benomyl, carbendazim, diethofencarb, fuberidazole,        pencycuron, thiabendazole thiophanate-methyl, zoxamide;    -   B3) a compound capable to inhibit the respiration for example    -   as CI-respiration inhibitor like diflumetorim;    -   as CII-respiration inhibitor like boscalid, carboxin, fenfuram,        flutolanil, furametpyr, mepronil, oxycarboxine, penthiopyrad,        thifluzamide;    -   as CIII-respiration inhibitor like azoxystrobin, cyazofamid,        dimoxystrobin, enestrobin, famoxadone, fenamidone,        fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,        pyraclostrobin, picoxystrobin, trifloxystrobin;    -   B4) a compound capable of to act as an uncoupler like dinocap,        fluazinam;    -   B5) a compound capable to inhibit ATP production like fentin        acetate, fentin chloride, fentin hydroxide, silthiofam;    -   B6) a compound capable to inhibit AA and protein biosynthesis        like andoprim, blasticidin-S, cyprodinil, kasugamycin,        kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;    -   B7) a compound capable to inhibit the signal transduction like        fenpiclonil, fludioxonil, quinoxyfen;    -   B8) a compound capable to inhibit lipid and membrane synthesis        like chlozolinate, iprodione, procymidone, vinclozolin,        pyrazophos, edifenphos, iprobenfos (IBP), isoprothiolane,        tolclofos-methyl, biphenyl, iodocarb, propamocarb,        propamocarb-hydrochloride;    -   B9) a compound capable to inhibit ergosterol biosynthesis like        fenhexamid, azaconazole, bitertanol, bromuconazole,        cyproconazole, diclobutrazole, difenoconazole, diniconazole,        diniconazole-M, epoxiconazole, etaconazole, fenbuconazole,        fluquinconazole, flusilazole, flutriafol, furconazole,        furconazole-cis, hexaconazole, imibenconazole, ipconazole,        metconazole, myclobutanil, paclobutrazol, penconazole,        propiconazole, prothioconazole, simeconazole, tebuconazole,        tetraconazole, triadimefon, triadimenol, triticonazole,        uniconazole, voriconazole, imazalil, imazalil sulfate,        oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox,        triforine, pefurazoate, prochloraz, triflumizole, viniconazole,        aldimorph, dodemorph, dodemorph acetate, fenpropimorph,        tridemorph, fenpropidin, spiroxamine, naftifine, pyributicarb,        terbinafine;    -   B10) a compound capable to inhibit cell wall synthesis like        benthiavalicarb, bialaphos, dimethomorph, flumorph,        iprovalicarb, polyoxins, polyoxorim, validamycin A;    -   B11) a compound capable to inhibit melanine biosynthesis like        carpropamid, diclocymet, fenoxanil, phtalide, pyroquilon,        tricyclazole;    -   B12) a compound capable to induce a host defence like        acibenzolar-S-methyl, probenazole, tiadinil;    -   B13) a compound capable to have a multisite action like        captafol, captan, chlorothalonil, copper preparations such as        copper hydroxide, copper naphthenate, copper oxychloride, copper        sulphate, copper oxide, oxine-copper and Bordeaux mixture,        dichlofluanid, dithianon, dodine, dodine free base, ferbam,        fluorofolpet, folpet, guazatine, guazatine acetate,        iminoctadine, iminoctadine albesilate, iminoctadine triacetate,        mancopper, mancozeb, maneb, metiram, metiram zinc, propineb,        sulphur and sulphur preparations including calcium polysulphide,        thiram, tolylfluanid, zineb, ziram;    -   B14) a compound selected in the following list: amibromdole,        benthiazole, bethoxazin, capsimycin, carvone, chinomethionat,        chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet,        debacarb, diclomezine, dichlorophen, dicloran, difenzoquat,        difenzoquat methylsulphate, diphenylamine, ethaboxam, ferimzone,        flumetover, flusulfamide, fosetyl-aluminium, fosetyl-calcium,        fosetyl-sodium, fluopicolide, fluoroimide, hexachlorobenzene,        8-hydroxyquinoline sulfate, irumamycin, methasulphocarb,        metrafenone, methyl isothiocyanate, mildiomycin, natamycin,        nickel dimethyldithiocarbamate, nitrothal-isopropyl,        octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and        salts, 2-phenylphenol and salts, phosphorous acid and its salts,        piperalin, propanosine-sodium, proquinazid, pyrrolnitrine,        quintozene, tecloftalam, tecnazene, triazoxide, trichlamide,        zarilamid and 2,3,5,6-tetrachloro-4-(methylsulfonyl)-pyridine,        N-(4-Chloro-2-nitrophenyl)-N-ethyl-4-methyl-benzenesulfonamide,        2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,        2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridincarboxamide,        3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,        cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)-cycloheptanol,        methyl        1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,        3,4,5-trichloro-2,6-pyridinedicarbonitrile, Methyl        2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyl]-.alpha.-(methoxymethylene)-benzeneacetate,        4-Chloro-alpha-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-benzeneacetamide,        (2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]-butanamide,        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,        5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,        N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicotinamide,        2-butoxy-6-iodo-3-propyl-benzopyranon-4-one,        N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,        N-(3-ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy-benzamide,        2-[[[[1-[3(1Fluoro-2-phenylethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alphaE-benzeneacetamide,        N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,        N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,        2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,        1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylic        acid,        O-[1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioic        acid.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound may also beparticularly advantageous. Examples of suitable bactericide mixingpartners may be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The compound of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops. Thus, according to a furtheraspect of the invention, there is provided a method for curatively orpreventively controlling the phytopathogenic fungi of plants or cropscharacterised in that a compound of formula (I) or a fungicidecomposition according to the invention is applied to the seed, the plantor to the fruit of the plant or to the soil wherein the plant is growingor wherein it is desired to grow.

In the same manner, the compound of formula (I) and the insecticidecomposition according to the invention can be used to curatively orpreventively control damaging insects, notably of plants or crops. Thus,according to a further aspect of the invention, there is provided amethod for curatively or preventively controlling damaging insects,notably of plants or crops, characterised in that a compound of formula(I) or an insecticide composition according to the invention is appliedto the seed, the plant or to the fruit of the plant or to the soilwherein the plant is growing or wherein it is desired to grow.

The method of treatment according to the invention may also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention may be made of cotton; flax; vine; fruit or vegetablecrops such as Rosaceae sp. (for instance pip fruit such as apples andpears, but also stone fruit such as apricots, almonds and peaches),Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp.,Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceaesp., Musaceae sp. (for instance banana trees and plantins), Rubiaceaesp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons,oranges and grapefruit); Solanaceae sp. (for instance tomatoes),Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp.,Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp.(for instance peas), Rosaceae sp. (for instance strawberries); majorcrops such as Graminae sp. (for instance maize, lawn or cereals such aswheat, rice, barley and triticale), Asteraceae sp. (for instancesunflower), Cruciferae sp. (for instance colza), Fabacae sp. (forinstance peanuts), Papilionaceae sp. (for instance soybean), Solanaceaesp. (for instance potatoes), Chenopodiaceae sp. (for instance beetroots)horticultural and forest crops; as well as genetically modifiedhomologues of these crops.

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention may be made of:

Powdery mildew diseases such as:

-   -   Blumeria diseases, caused for example by Blumeria graminis;    -   Podosphaera diseases, caused for example by Podosphaera        leucotricha;    -   Sphaerotheca diseases, caused for example by Sphaerotheca        fuliginea;    -   Uncinula diseases, caused for example by Uncinula necator;

Rust diseases such as:

-   -   Gymnosporangium diseases, caused for example by Gymnosporangium        sabinae;    -   Hemileia diseases, caused for example by Hemileia vastatrix;    -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi        or Phakopsora meibomiae;    -   Puccinia diseases, caused for example by Puccinia recondita;    -   Uromyces diseases, caused for example by Uromyces        appendiculatus;

Oomycete diseases such as:

-   -   Bremia diseases, caused for example by Bremia lactucae;    -   Peronospora diseases, caused for example by Peronospora pisi        or P. brassicae;    -   Phytophthora diseases, caused for example by Phytophthora        infestans;    -   Plasmopara diseases, caused for example by Plasmopara viticola;    -   Pseudoperonospora diseases, caused for example by        Pseudoperonospora humuli or Pseudoperonospora cubensis;    -   Pythium diseases, caused for example by Pythium ultimum;

Leafspot, leaf blotch and leaf blight diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria solani;    -   Cercospora diseases, caused for example by Cercospora beticola;    -   Cladiosporum diseases, caused for example by Cladiosporium        cucumerinum;    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus;    -   Colletotrichum diseases, caused for example by Colletotrichum        lindemuthanium;    -   Cycloconium diseases, caused for example by Cycloconium        oleaginum;    -   Diaporthe diseases, caused for example by Diaporthe citri;    -   Elsinoe diseases, caused for example by Elsinoe fawcettii;    -   Gloeosporium diseases, caused for example by Gloeosporium        laeticolor;    -   Glomerella diseases, caused for example by Glomerella cingulata;    -   Guignardia diseases, caused for example by Guignardia bidwelli;    -   Leptosphaeria diseases, caused for example by Leptosphaeria        maculans; Leptosphaeria nodorum;    -   Magnaporthe diseases, caused for example by Magnaporthe grisea;    -   Mycosphaerella diseases, caused for example by Mycosphaerella        graminicola; Mycosphaerella arachidicola; Mycosphaerella        fijiensis;    -   Phaeosphaeria diseases, caused for example by Phaeosphaeria        nodorum;    -   Pyrenophora diseases, caused for example by Pyrenophora teres;    -   Ramularia diseases, caused for example by Ramularia collo-cygni;    -   Rhynchosporium diseases, caused for example by Rhynchosporium        secalis;    -   Septoria diseases, caused for example by Septoria apii or        Septoria lycopercisi;    -   Typhula diseases, caused for example by Typhula incamata;    -   Venturia diseases, caused for example by Venturia inaequalis;

Root and stem diseases such as:

-   -   Corticium diseases, caused for example by Corticium graminearum;    -   Fusarium diseases, caused for example by Fusarium oxysporum;    -   Gaeumannomyces diseases, caused for example by Gaeumannomyces        graminis;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Tapesia diseases, caused for example by Tapesia acuformis;    -   Thielaviopsis diseases, caused for example by Thielaviopsis        basicola;

Ear and panicle diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria spp.    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Cladosporium diseases, caused for example by Cladosporium spp.    -   Claviceps diseases, caused for example by Claviceps purpurea;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Monographella diseases, caused for example by Monographella        nivalis;

Smut and bunt diseases such as:

-   -   Sphacelotheca diseases, caused for example by Sphacelotheca        reiliana;    -   Tilletia diseases, caused for example by Tilletia caries;    -   Urocystis diseases, caused for example by Urocystis occulta;    -   Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

-   -   Aspergillus diseases, caused for example by Aspergillus flavus:    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Penicillium diseases, caused for example by Penicillium        expansum;    -   Sclerotinia diseases, caused for example by Sclerotinia        sclerotiorum;    -   Verticilium diseases, caused for example by Verticilium        alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

-   -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Phytophthora diseases, caused for example by Phytophthora        cactorum;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Sclerotium diseases, caused for example by Sclerotium rolfsii;    -   Microdochium diseases, caused for example by Microdochium        nivale;

Canker, broom and dieback diseases such as:

-   -   Nectria diseases, caused for example by Nectria galligena;

Blight diseases such as:

-   -   Monilinia diseases, caused for example by Monilinia laxa;

Leaf blister or leaf curl diseases such as:

-   -   Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

-   -   Esca diseases, caused for example by Phaemoniella clamydospora;    -   Eutypa dyeback, caused for example by Eutypa late;    -   Dutch elm disease, caused for example by Ceratocystsc ulmi;

Diseases of flowers and Seeds such as:

-   -   Botrytis diseases, caused for example by Botrytis cinerea;

Diseases of tubers such as:

-   -   Rhizoctonia diseases, caused for example by Rhizoctonia solani.

Among the damaging pests or insects that can be controlled at anydevelopment stage according to the insecticide method of the invention,mention may be made to:

-   -   the order of the Anoplura (Phthiraptera), for example, Damalinia        spp., Haematopinus spp., Linognathus spp., Pediculus spp.,        Trichodectes spp.;    -   the class of the Arachnida, for example, Acarus siro, Aceria        sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,        Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes        spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus        pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp.,        Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus        spp., Oligonychus spp., Ornithodoros spp., Panonychus spp.,        Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes        spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,        Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp.,        Tetranychus spp., Vasates lycopersici;    -   the class of the Bivalva, for example, Dreissena spp.;    -   the order of the Chilopoda, for example, Geophilus spp.,        Scutigera spp.;    -   the order of the Coleoptera, for example, Acanthoscelides        obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,        Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,        Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp.,        Attagenus spp., Bruchidius obtectus, Bruchus spp.,        Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,        Cosmopolites spp., Costelytra zealandica, Curculio spp.,        Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp.,        Epilachna spp., Faustinus cubae, Gibbium psylloides,        Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus,        Hypera postica, Hypothenemus spp., Lachnosterna consanguinea,        Leptino-tarsa decemlineata, Lissorhoptrus oryzophilus, Lixus        spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,        Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus        hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis,        Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae,        Phyllophaga spp., Popillia japonica, Premnotrypes spp.,        Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis,        Rhizopertha dominica, Sitophilus spp., Sphenophorus spp.,        Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium        spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus        spp.    -   the order of the Collembola, for example, Onychiurus armatus;    -   the order of the Dermaptera, for example, Forficula auricularia;    -   the order of the Diplopoda, for example, Blaniulus guttulatus;    -   the order of the Diptera, for example, Aedes spp., Anopheles        spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis        capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia        anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,        Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus        spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza        spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,        Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp.,        Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp;    -   the class of the Gastropoda, for example, Arion spp.,        Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp.,        Lymnaea spp., Oncomelania spp., Succinea spp.;    -   the class of the helminths, for example, Ancylostoma duodenale,        Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma        spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia        timori, Bunostomum spp., Chabertia spp., Clonorchis spp.,        Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria,        Diphyllobothrium latum, Dracunculus medinensis, Echinococcus        granulosus, Echinococcus multilocularis, Enterobius        vermicularis, Faciola spp., Haemonchus spp., Heterakis spp.,        Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp.,        Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus,        Ostertagia spp., Paragonimus spp., Schistosomen spp,        Strongyloides fuelleborni, Strongyloides stercoralis,        Stronyloides spp., Taenia saginata, Taenia solium, Trichinella        spiralis, Trichinella nativa, Trichinella britovi, Trichinella        nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp.,        Trichuris trichuria, Wuchereria bancrofti;    -   Protozoa, such as Eimeria;    -   the order of the Heteroptera, for example, Anasa tristis,        Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma        livida, Cavelerius spp., Cimex spp., Creontiades dilutus,        Dasynus piperis, Dichelops furcatus, Diconocoris hewetti,        Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis        spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus        phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp.,        Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,        Psallus seriatus, Pseudacysta persea, Rhodnius spp.,        Sahlbergella singularis, Scotinophora spp., Stephanitis nashi,        Tibraca spp., Triatoma spp;    -   the order of the Homoptera, for example, Acyrthosipon spp.,        Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus        barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,        Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia        apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp.,        Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii,        Brachycolus spp., Brevicoryne brassicae, Calligypona marginata,        Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,        Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis        tegalensis, Chlorita onukii, Chromaphis juglandicola,        Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,        Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,        Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp.,        Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp.,        Erythroneura spp., Euscelis bilobatus, Geococcus coffeae,        Homalodisca coagulate, Hyalopterus arundinis, lcerya spp.,        Idiocerus spp., Idioscopus spp., Laodelphax striatellus,        Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum        spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella        spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis        pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp.,        Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,        Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus        spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus        passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis        aspidistrae, Planococcus spp., Protopulvinaria pyriformis,        Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp.,        Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada        gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,        Scaphoides titanus, Schizaphis graminum, Selenaspidus        articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp.,        Stictocephala festina, Tenalaphara malayensis, Tinocallis        caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes        vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus        vitifolii;    -   the order of the Hymenoptera, for example, Diprion spp.,        Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.;    -   the order of the Isopoda, for example, Armadillidium vulgare,        Oniscus asellus, Porcellio scaber;    -   the order of the Isoptera, for example, Reticulitermes spp.,        Odontotermes spp.;    -   the order of the Lepidoptera, for example, Acronicta major,        Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia        spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus        piniarius, Cacoecia podana, Capua reticulana, Carpocapsa        pomonella, Cheimatobia brumata, Chilo spp., Choristoneura        fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias        insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa        spp., Feltia spp., Galleria mellonella, Helicoverpa spp.,        Heliothis spp., Hofmannophila pseudospretella, Homona magnanima,        Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella,        Lithophane antennata, Loxagrotis albicosta, Lymantria spp.,        Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna        separate, Oria spp., Oulema oryzae, Panolis flammea,        Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp.,        Plutella xylostella, Prodenia spp., Pseudaletia spp.,        Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp.,        Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella,        Tortrix viridana, Trichoplusia spp.;    -   the order of the Orthoptera, for example, Acheta domesticus,        Blatta orientalis, Blattella germanica, Gryllotalpa spp.,        Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta        americana, Schistocerca gregaria;    -   the order of the Siphonaptera, for example, Ceratophyllus spp.,        Xenopsylla cheopis.    -   the order of the Symphyla, for example, Scutigerella immaculate;    -   the order of the Thysanoptera, for example, Baliothrips        biformis, Enneothrips flavens, Frankliniella spp., Heliothrips        spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips        cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips        spp.;    -   the order of the Thysanura, for example, Lepisma saccharine;    -   the phytoparasitic nematodes including for example, Anguina        spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus        spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus        spp., Heterodera spp., Longidorus spp., Meloidogyne spp.,        Pratylenchus spp., Radopholus similis, Rotylenchus spp.,        Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp.,        Tylenchulus semipenetrans, Xiphinema spp;    -   the beetles, such as Hylotrupes bajulus, Chlorophorus pilosis,        Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis,        Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus        brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis,        Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis,        Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus        capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus        minutus;    -   Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus        gigas taignus, Urocerus augur;    -   termites, such as Kalotermes flavicollis, Cryptotermes brevis,        Heterotermes indicola, Reticulitermes flavipes, Reticulitermes        santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,        Zootermopsis nevadensis, Coptotermes formosanus;    -   Bristletails, such as Lepisma saccharina;    -   the order of the Acarina, for example, Argas persicus, Argas        reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus        domesticus, Ornithodorus moubat, Rhipicephalus sanguineus,        Trombicula alfreddugesi, Neutrombicula autumnalis,        Dermatophagoides pteronissimus, Dermatophagoides forinae;    -   the order of the Araneae, for example, Avicularlidae, Araneidae;    -   the order of the Opiliones, for example, Pseudoscorpiones        chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium;    -   the order of the Isopoda, for example, Oniscus asellus,        Porcellio scaber;    -   the order of the Diplopoda, for example, Blaniulus guttulatus,        Polydesmus spp.;    -   the order of the Chilopoda, for example, Geophilus spp.;    -   the order of the Zygentoma, for example, Ctenolepisma spp.,        Lepisma saccharine, Lepismodes inquilinus;    -   the order of the Blattaria, for example, Blatta orientalies,        Blattella germanica, Blattella asahinai, Leucophaea maderae,        Panchlora spp., Parcoblatta spp., Periplaneta australasiae,        Periplaneta americana, Periplaneta brunnea, Periplaneta        fuliginosa, Supella longipalpa;    -   the order of the Saltatoria, for example, Acheta domesticus;    -   the order of the Dermaptera, for example, Forficula auricularia;    -   the order of the Isoptera, for example, Kalotermes spp.,        Reticulitermes spp;    -   the order of the Psocoptera, for example, Lepinatus spp.,        Liposcelis spp;    -   the order of the Coleoptera, for example, Anthrenus spp.,        Attagenus spp., Dermestes spp.; Latheticus oryzae, Necrobia        spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius,        Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.    -   the order of the Diptera, for example, Aedes aegypti, Aedes        albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora        erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus,        Culex pipiens, Culex tarsalis, Drosophila spp., Fannia        canicularis, Musca domestica, Phlebotomus spp., Sarcophaga        camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa;    -   the order of the Lepidoptera, for example, Achroia grisella,        Galleria mellonella, Plodia interpunctella, Tinea cloacella,        Tinea pellionella, Tineola bisselliella;    -   the order of the Siphonaptera, for example, Ctenocephalides        canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans,        Xenopsylla cheopis.    -   the order of the Hymenoptera, for example, Camponotus        herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,        Monomorium pharaonis, Paravespula spp., Tetramorium caespitum;    -   the order of the Anoplura, for example, Pediculus humanus        capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera        vastatrix, Phthirus pubis;    -   the order of the Heteroptera, for example, Cimex hemipterus,        Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The fungicide or insecticide composition according to the invention mayalso be used against fungal diseases or damaging insects liable to growor attack on or inside timber. The term “timber” means all types ofspecies of wood, and all types of working of this wood intended forconstruction, for example solid wood, high-density wood, laminated wood,and plywood. The method for treating timber according to the inventionmainly consists in contacting one or more compounds according to theinvention, or a composition according to the invention; this includesfor example direct application, spraying, dipping, injection or anyother suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The fungicide composition according to the invention may also be used inthe treatment of genetically modified organisms with the compoundsaccording to the invention or the agrochemical compositions according tothe invention. Genetically modified plants are plants into genome ofwhich a heterologous gene encoding a protein of interest has been stablyintegrated. The expression “heterologous gene encoding a protein ofinterest” essentially means genes which give the transformed plant newagronomic properties, or genes for improving the agronomic quality ofthe modified plant.

The compounds or mixtures according to the invention may also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following tables of compounds and examples. Thefollowing tables illustrate in a non-limiting manner examples ofcompounds according to the invention.

In the following examples, M+1 (or M−1) means the molecular ion peak,plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed inmass spectroscopy and M (Apcl+) means the molecular ion peak as it wasfound via positive atmospheric pressure chemical ionisation in massspectroscopy.

In the following examples, the logP values were determined in accordancewith EEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using linear alkan-2-ones (comprising 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 190 nm to 400 nm.

TABLE 1

log p No R2 R3 R1 R4 R5 R7 R8 (HCOOH) 1.1 Me Et H Me Me Cl Cl 2.12 1.2Me Et H Me Me —CH═CH—C(Cl)═CH— 2.29 1.3 Me iPr H Me Me Cl Cl 2.18 1.4 MeEt H Me Me tBu Cl 2.76 1.5 Me Et H Me Me CF3 Cl 2.15 1.6 Me Et H Me MeCl Br 2.00 1.7 —CH2CH2CH2CH2CH2— H Me Me Cl Cl 2.23 1.8 Me Et H Me Me—CH═CH—CH═CH— 1.89 1.9 Me iPr H Me Me iPr Cl 2.57 1.10 Me iPr H Me MeCF3 Cl 2.29 1.11 Me iPr H Me Me Cl Br 2.22 1.12 Me Et H Me Me Me Cl 1.981.13 Me iPr H Me Me Me Cl 2.14 1.14 Me iPr H Me Me Cl H 1.70 1.15 Men-Pr H Me Me —CH═CH—C(Cl)═CH— 2.46 1.16 Me Et H Me Me Me CMe═NO-t-Bu2.80 1.17 Me Et H Me Me Cl Me 1.80 1.18 Me Et H Me Me Cl H 1.60 1.19 MeEt H Me Me Me CMe═NOMe 1.97 1.20 Me Et H Me Me iPr Cl 2.52 1.21 Me Et HMe Me Me CMe═NO—CH2CH═CH2 2.33 1.22 —CH2CH2CH2CH2CH(CH3)— H Me Me Cl Cl2.44 1.23 Me iPr H Me Me Cl Me 1.94 1.24 Me Et H Me Me Me CMe═NOCH(Me)Ph2.87 1.25 H —CH2CH2CH2CH2— Me Me Cl Cl 1.97 1.26 —CH2CH2CH2CH2— H Me MeCl Cl 2.12 1.27 Me Et H Me Me Me Ac 1.50 1.28 Me iPr H Me H Cl Cl 2.091.29 Me n-Pr H Me Me —CH═CH—CH═CH— 2.04 1.30 —CH2CH2—O—CH2CH2— H Me MeCl Cl 1.95 1.31 Me Me H Me Me Cl Me 1.69 1.32 H —CH2CH2CH2— Me Me Cl Cl1.93 1.33 Me Et H Me H Me Me 1.65 1.34 Me iPr H Me H Me Me 1.66 1.35 MeiPr H Me Me Me nPr 2.29 1.36 Me Et H Me Me Me nPr 2.22 1.37 Me iPr H MeMe Me Me 1.98 1.38 Me Et H Me Me Me Me 1.87 1.39 Me Et H Me H Cl Cl 1.991.40 Me Et H Me Me Me CMe═NOH 1.55 1.41 Me iPr H Me Me Me CMe═NOH 1.661.42 Me Et H Me Me CHO Cl 1.46 1.43 Me Et H Me Me CH═NOMe Cl 1.93 1.44Me Et H Me Me CH═NO-t-Bu Cl 2.65 1.45 Me Et H Me Me CH═NO—CH2CH═CH2 Cl2.26 1.46 Me Et H Me Me CH═NO-Et Cl 2.17 1.47 Me Et H Me Me CH═NO—CH2-PhCl 2.51 1.48 Me Et H Me Me CMe═NOCH(Me)Ph Cl 2.75 1.49 Me Et H Me MeCH═NO—CH2-(4-t-Bu)-Ph Cl 3.46 1.50 Me Et H Me Me CH═NO—CH2-(4-NO2)-Ph Cl2.60 1.51 Me Et H Me Me CH═NO—CH2-(3-Me)-Ph Cl 2.84 1.52 Me Et H Me MeCH═NO—CH2-(3-Cl)-Ph Cl 2.86 1.53 Me Et H Me Me CH═NO—CH2-(4-CF3)-Ph Cl3.01 1.54 Me Et H Me Me CH═NO—CH2-(3-CF3)-Ph Cl 2.97 1.55 Me Et H Me MeCl 4-Cl-Ph 2.80 1.56 Me iPr H Me Me Cl 4-Cl-Ph 3.00 1.57 Me Et H Me MeCl CH═NOMe 2.04 1.58 Me Et H Me Me Cl CH═NO—CH2CH═CH2 2.32 1.59 Me Et HMe Me Cl CH═NO—CH2-Ph 2.64 1.60 Me Et H Me Me Ph H 2.18 1.61 Me iPr H MeMe Ph H 2.25 1.62 Me Et H Me Me Cl CHO 1.68 1.63 Me Et H Me Me CH═NOH Cl1.53 1.64 Me iPr H Me Me tBu Cl 2.79 1.65 —CH2CH2CH2CH2CH2— H Me Me tBuCl 3.05 1.66 —CH2CH2CH2CH2CH2— H Me Me Cl 4-Cl-Ph 2.97 1.67 Me Et H MeMe —CCl═CH—CH═CH 2.17 1.68 —CH2CH2CH2CH2CH2— H Me Me —CCl═CH—CH═CH 2.341.69 Me nPr H Me Me —CCl═CH—CH═CH 2.29 1.70 Me iPr H Me Me —CCl═CH—CH═CH2.40 1.71 Me Et H Me Me tBu Br 2.78 1.72 Me Et H Me Me CN Cl 1.74 1.73Me Et H Me Me Cl tBu 2.87 1.74 Me Et H Me Me H tBu 2.18 1.75 Me Et H MeMe tBu H 2.26

TABLE 2

logP No R1 R2 R3 R4 R5 R9 (HCOOH) 2.1 H Me i-Pr Me H i-Pr 1.77 2.2 H MeEt Me H i-Pr 1.57 2.3 H Me Et Me Me i-Pr 1.74 2.4 H Me i-Pr Me Me i-Pr1.89 2.5 H Me Et Me Me Cl 1.56 2.6 H Me i-Pr Me Me Cl 1.67 2.7 H Me EtMe H t-Bu 2.04

TABLE 3

logP No R1 R2 R3 R4 R5 R10 (HCOOH) 3.1 H Me i-Pr Me Me CF3 1.84 3.2 H MeEt Me Me CF3 1.78 3.3 H Me Et Me Me Ph 1.93 3.4 H Me Et Me Me2-F-6-OMe-Ph 1.87 3.5 H Me Et Me Me 2-F-Ph 1.98 3.6 H Me i-Pr Me Me Ph2.00 3.7 H Me Et Me Me 3-F-4-F-Ph 2.08 3.8 H Me Et Me Me 4-OCF₃-Ph 2.353.9 H Me i-Pr Me Me 4-OCF₃-Ph 2.48 3.10 H Me Et Me Me 2-F-4-CF₃-Ph 2.333.11 H Me i-Pr Me Me 2-F-4-CF₃-Ph 2.43 3.12 H Me Et Me Me 4-SO₂Me-Ph1.52 3.13 H Me i-Pr Me Me 3-F-4-F-Ph 2.28 3.14 H Me i-Pr Me Me 2-F-Ph2.22 3.15 H Me i-Pr Me Me 2-F-6-OMe-Ph 2.11 3.16 H Me i-Pr Me Me4-SO₂Me-Ph 1.69 3.17 H Me i-Pr Me Me 2-Cl-Ph 2.11 3.18 H Me i-Pr Me MeSMe 1.82 3.19 H Me i-Pr Me Me i-Pr 1.69 3.20 H Me Et Me Me 2-Cl-Ph 2.053.21 H Me Et Me Me SMe 1.69 3.22 H Me Et Me Me i-Pr 1.61 3.23 H Me Et MeMe cyclo-Pr 1.50 3.24 H Me Et Me Me 3-Cl-4-F-Ph 2.13 3.25 H Me i-Pr MeMe 4-MeO-Ph 2.02 3.26 H Me i-Pr Me Me 3-MeO-Ph 2.06 3.27 H Me i-Pr Me Me3-Me-Ph 2.12 3.28 H Me Et Me Me 4-NO₂-Ph 1.92 3.29 H Me Et Me Me4-MeO-Ph 1.93 3.30 H Me Et Me Me 3-MeO-Ph 2.02 3.31 H Me Et Me Me3-Me-Ph 2.06 3.32 H Me i-Pr Me Me cyclo-Pr 1.57 3.33 H Me i-Pr Me Me4-NO₂-Ph 2.05 3.34 H Me i-Pr Me Me 3-Cl-4-F-Ph 2.27 3.35 H—CH2CH2CH2CH2— Me Me 4-OCF₃-Ph 2.64 3.36 H —CH2CH2CH2CH2— Me Me2-F-4-CF₃-Ph 2.61 3.37 H —CH2CH2CH2CH2— Me Me 3-Me-Ph 2.21 3.38 H—CH2CH2CH2CH2— Me Me 2-F-Ph 2.19 3.39 H —CH2CH2CH2CH2— Me Me 2-Cl-Ph2.21 3.40 H —CH2CH2CH2CH2— Me Me SMe 1.89 3.41 H —CH2CH2CH2CH2— Me Mei-Pr 1.73 3.42 H —CH2CH2CH2CH2— Me Me 3-Cl-4-F-Ph 2.43 3.43 H—CH2CH2CH2CH2— Me Me cyclo-Pr 1.65 3.44 —CH2CH2CH2— H Me Me CF3 1.59

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

PREPARATION EXAMPLE 1 Process (a)—compound (IV) to compound (II):4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline-intermediate(II-1)

1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to asolution of 4.1 g (30.0 mmol) of 4-amino-2,5-dimethylphenol in 30 ml ofdimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol)of 2,4,5-trichloro-1,3-thiazole were added and the reaction mixture wasstirred for 1 h at 100° C. At ambient temperature 0.5 ml methanol, 10 mlof water and 100 ml of ethyl acetate were added successively. Theorganic layer was separated, the watery layer extracted with ethylacetate and the combined organic layers were dried over magnesiumsulfate. Concentration in vacuo and column chromatographie (petroleumether/acetone 4/1) yielded 4.8 g (16.6 mmol, 55%) of4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline log P(pH=2.3)=3.4

PREPARATION EXAMPLE 2 Process (b2)—compound (II) to compound (I):N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide-compound1.1

To a mixture of 2.0 g (6.9 mmol) of4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline in 2.5 mltoluene a solution of 9.7 mmol of N-(dimethoxymethyl)-N-methylethanamine(60% in methanol) was added. The reaction mixture was stirred for 16 hrsat 105° C. The reaction mixture was concentrated in vacuo. Columnchromatographie (gradient: cyclohexane->ethyl acetate) yielded 2.4 g(6.7 mmol) 97% ofN′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide;log P (pH 2.3)=2.04

PREPARATION EXAMPLE 3 Process (b3)—compound (II) to compound (I):N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methlimidoformamide-compound1.1

To a mixture of 2.0 g (6.9 mmol) of4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline and 11.3 ml(0.13 mol) of trimethoxymethane 0.12 g (0.7 mmol) of p-toluene sulfonicacid were added. The reaction mixture was refluxed for 16 hrs andconcentrated in vacuo. The crude product was solved in 12 ml of tolueneand 0.82 g (13.8 mmol) N-methylethanamine were added. The reactionmixture was stirred for 16 hrs at 50° C. The reaction mixture wasconcentrated in vacuo. Column chromatographie (gradient: petroleumether->methyl-tert. butyl ether) yielded 2.3 g (6.3 mmol) 91% ofN′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide;log P (pH 2.3)=2.04

PREPARATION EXAMPLE 4 Process (b1)—compound (II) to compound (I):4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-lidene]aniline-compound1.25

A solution of 0.2 g (1.5 mmol) of phosphoric trichloride in 5 ml toluenewas added to a mixture of 0.3 g (3.0 mmol) of piperidin-2-one, theexothermic reaction was stirred for 2 hrs at ambient temperature. Then asolution of 0.43 g (1.5 mmol) of4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline in 5 ml oftoluene was added and the reaction mixture was refluxed for 5 hrs. Atambient temperature 5 ml of a 10% aqueous solution of sodium hydroxidewas added. Separation of the layers, extraction of the watery layer with10 ml of toluene, drying over magnesium sulfate, concentration in vacuoand Column chromatographie (gradient: cyclohexane->ethyl acetate)yielded 0.55 g (1.5 mmol) 99% of4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethyl-N-[piperidin-2-lidene]aniline;log P (pH 2.3)=1.97

PREPARATION EXAMPLE 5 Process (c)—compound (I) to compound (I):N′-(4-{([5-(N-allylethanimidoyl)-4-methyl-1,3-thiazol-2-yl]oxyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide-compound1.21

A solution of 0.3 g (0.87 mmol) ofN′-{4-[(5-acetyl-4-methyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamideand 0.095 g (0.87 mmol) of 3-(aminooxy)prop-1-ene hydrochloride in asolvent mixture of 10 ml of methanol and 3 ml of water was stirred atambient temperature for 5 days. Then the mixture was diluted with waterand dichloromethane was added. Separation of the layers, extraction ofthe water phase with dichloromethane, drying of the organic layer oversodium sulfate end evaporation of the solvent yielded 0.14 g (0.29 mmol)33% ofN′-(4-{[5-(N-allylethanimidoyl)-4-methyl-1,3-thiazol-2-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamideas a mixture of two stereoisomers; log P (pH 2.3)=2.15 and 2.33.

PREPARATION EXAMPLE 5 Process (b3)—compound (III) to compound (IX):N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide-intermediate(IX-a)

To a mixture of 10.0 g (73 mmol) of 4-amino-2,5-dimethylphenol and 73 ml(0.84 mol) of trimethoxymethane 0.73 g (4.2 mmol) of p-toluene sulfonicacid were added and the mixture was heated to reflux for 2 hours. Thenthe volatiles were removed in vacuo and the residue was dissolved in 73ml of toluene and 12.9 g (217 mmol) N-methylethanamine were added. Thereaction mixture was heated to 50° C. for 20 hrs and concentrated invacuo. Column chromatographie (gradient: cyclohexane->ethyl acetate)yielded 9.17 g (44 mmol) 55% ofN-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide; log P(pH 2.3)=0.41.

PREPARATION EXAMPLE 6 Process (a)—compound (IV) and compound (IX) tocompound (I):N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide-compound1.42

To a solution of 3.57 g (17 mmol) ofN-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide in 60ml of DMF were added 2.51 g (18 mmol) of potassium carbonate and themixture was stirred at ambient temperature for 30 min. Then 3.00 g (16.5mmol) of 2,5-dichloro-1,3-thiazole-4-carbaldehyde were added and themixture was stirred at ambient temperature for 7 days. Then the reactionmixture was poured on water, dichloromethane and some NaCl was added,layers were separated, the water layer was extracted withdichloromethane, the organic phase was dried over sodium sulfate andevaporated. Column chromatographic (gradient: dichloromethane->methanol)yielded 4.40 g (12.5 mmol) 67% ofN′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamidelog P (pH 2.3)=1.51

PREPARATION EXAMPLE 7 Process (c):N′-[4-({4-[(tert-butoxyimino)methyl]-5-chloro-1,3-thiazol-2-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide-compound1.44

A solution of 0.23 g (0.50 mmol) ofN′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamideand 63 mg (0.50 mmol) of 2-(aminooxy)-2-methylpropane hydrochloride in asolvent mixture of 10 ml of methanol and 3 ml of water was stirred atambient temperature for 5 days. Evaporation of the solvents and columnchromatography of the crude mixture (gradient cyclohexane->ethylacetate) yielded 130 mg (0.37 mmol) 61% ofN′-[4-({4-[(tert-butoxyimino)methyl]-5-chloro-1,3-thiazol-2-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide.Log P (pH 2.3)=2.65

EFFICACY EXAMPLE A In vivo Preventive Test on Puccinia recondita f. Sp.tritici (Wheat Brown Rust)

Solvent: 50 parts by weight of N,N-dimethylacetamid Emulsifier:  1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are inoculated with aspore suspension of Puccinia recondita in a 0.1% strength aqueous agarsolution. After the spray coating has dried on, the plants are sprayedwith the preparation of active compound at the stated rate ofapplication. The plants remain for 24 hours in an incubation cabinet at20° C. and a relative atmospheric humidity of 100%.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80% topromote the development of rust pustules.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no disease is observed.

In this test the following compounds according to the invention showedan efficacy of 70% or even higher at a concentration of 1000 ppm ofactive ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10,1.11, 1.12, 1.13, 1.15, 1.17, 1.18, 1.20, 1.23, 1.28, 1.29, 1.63, 1.71,1.72, 1.73, 1.74, 1.75, 2.2, 2.3, 2.4, 2.7, 3.1, 3.2.

EFFICACY EXAMPLE B In Vivo Preventive Test on Erysiphe gramini (PowderyMildew on Barley)

Solvent: 50 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f. sp. hordei.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80% topromote the development of mildew pustules.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, while an efficacy of 100%means that no disease is observed.

In this test the following compounds according to the invention showedan efficacy of 70% or even higher at a concentration of 1000 ppm ofactive ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10,1.11, 1.12, 1.13, 1.17, 1.18, 1.20, 1.23, 1.28, 1.29, 2.2, 2.3, 2.4,3.1, 3.2.

EFFICACY EXAMPLE C In Vivo Protective Test on Alternaria solani (LeafSpot of Tomato)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Alternaria solani. The plants remain for oneday in an incubation cabinet at approximately 20° C. and a relativeatmospheric humidity of 100%. Then the plants are placed in anincubation cabinet at approximately 20° C. and a relative atmospherichumidity of 96%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the control while an efficacy of 100% meansthat no disease is observed.

In this test, invention related compounds of the following formularevealed an efficacy of 70% or higher at a concentration of 500 ppm ofactive ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.7, 1.7, 1.8, 1.9, 1.12,1.13, 1.14, 1.16, 1.17, 1.19, 1.20, 1.21, 1.24, 1.27, 1.63, 1.64, 1.65,1.66, 1.70, 1.71, 1.74, 2.3, 2.7, 3.2, 3.20, 3.21, 3.24, 3.31, 3.34,3.35, 3.39.

EFFICACY EXAMPLE D In Vivo Protective Test on Podosphaera leucotricha(Apples)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the causal agent of apple mildew(Podosphaera leucotricha). The plants are then placed in a greenhouse atapproximately 23° C. and a relative atmospheric humidity ofapproximately 70%.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no disease is observed.

In this test the compounds according to the invention of the followingstructures showed efficacy of 70% or even higher at a concentration of100 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8,1.9, 1.10, 1.11, 1.12, 1.15, 1.17, 1.18, 1.71, 1.72, 1.74, 1.75, 2.3,2.7.

EFFICACY EXAMPLE E In Vivo Protective Test on Sphaerotheca fuliginea(Cucumbers)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protect activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Sphaerotheca fuliginea. The plants are thenplaced in a greenhouse at approximately 23° C. and a relativeatmospheric humidity of approximately 70%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, while an efficacy of 100%means that no disease is observed.

In this test the compounds according to the invention of the followingstructures showed efficacy of 70% or even higher at a concentration of100 ppm of active ingredient: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8,1.9, 1.10, 1.11, 1.12, 1.15, 1.18, 1.21, 1.63, 2.3.

EFFICACY EXAMPLE F In Vivo Protective Test on Uromyces appendiculatus(Beans)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the causal agent of bean rust (Uromycesappendiculatus) and then remain for 1 day in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 100%.

The plants are then placed in a greenhouse at approximately 21° C. and arelative atmospheric humidity of approximately 90%.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no disease is observed.

In this test the compounds according to the invention of the followingstructures showed efficacy of 70% or even higher at a concentration of100 ppm of active ingredient: 1.2, 1.71, 1.72, 1.74, 1.75, 2.7.

EFFICACY EXAMPLE G Myzus persicae—Test: (MYZUPE Spray Application)

Solvent:  78 parts by weight acetone 1.5 parts by weightdimethylformamide Wetting agent: 0.5 parts by weightalkylarylpolyglcolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Chinese cabbage (Brassica pekinesis) leaf-disks infected with allinstars of the green peach aphid (Myzus persicae), are sprayed with apreparation of the active ingredient at the desired concentration.

After the specified period of time, mortality in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test for example, the following compounds from the preparationexamples showed good activity: 1.25

EFFICACY EXAMPLE H Heliotis virescens—Test on Heliotis virescens (HELIVISpray Application)

Solvent:  78 parts by weight acetone 1.5 parts by weightdimethylformamide Wetting agent 0.5 parts by weightalkylarylpolyglcolether

To produce a suitable preparation of the active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is dilutes with emulsifier-containingwater to the desired concentration.

Soybean (Glycine max.) leaf sections are sprayed with a preparation ofthe active ingredient of the desired concentration. Once dry, the leafsections are infested with eggs of cotton bollworm (Heliotis virescens).

After the specified period of time, mortality in % is determined. 100%means that all eggs have been killed and 0% means that none of the eggshave been killed.

In this test for example, the following compounds from the preparationexamples showed good activity: 1.11, 1.23, 1.25, 1.26.

The invention claimed is:
 1. A phenyl-amidine derivative of formula (I):

wherein R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl,a substituted or non substituted C₂-C₁₂-alkenyl, a substituted or nonsubstituted C₂-C₁₂-alkynyl, SH or a substituted or non substitutedS—C₁-C₁₂-alkyl; R² represents methyl; R³ represents a substituted or nonsubstituted C₂-C₁₂-alkyl, substituted or non substitutedC₃-C₆-cycloalkyl, substituted or non substituted C₂-C₁₂-alkenyl,substituted or non substituted C₂-C₁₂-alkynyl, halogeno-C₁-C₁₂-alkyl; orR¹ and R², R¹ and R³ or R² and R³ can form together a substituted or nonsubstituted 5- to 7-membered heterocycle; R⁴ represents a substituted ornon substituted C₁-C₁₂-alkyl, a halogen atom, halogeno-C₁-C₁₂-alkyl,substituted or non substituted 0-C₁-C₁₂-alkyl or cyano; R⁵ represents H,a substituted or non substituted C₁-C₁₂-alkyl, a halogen atom,halogeno-C₁-C₁₂-alkyl, substituted or non substituted O—C₁-C₁₂-alkyl orcyano; R⁶ represents a heterocycle selected from the group consisting of

wherein R⁷ represents H, halogen, nitro, cyano; substituted or nonsubstituted phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl, C₁-C₆-halogen-alkoxyor C₁-C₆-halogenalkylthio; C₁-C₈-alkyl-S(O)_(m)R¹¹;C₁-C₈-alkyl-SO₂NR¹²R¹³; C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹,SO₂NR¹²R¹³, COR¹⁴; R⁸ represents H, halogen, cyano; substituted or nonsubstituted phenyl, substituted or non substituted benzyl; C₁-C₈-alkyl,C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl, C₁-C₆-halogenalkoxyor C₁-C₆-halogenalkylthio; C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; R⁷and R⁸ can form a carbocycle, which can be saturated, unsaturated oraromatic and substituted or non substituted by halogen, C₁-C₄-alkyl,C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl; R⁹ represents H, halogen,cyano; phenyl substituted by F, Cl, Br, I, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; substituted or non substitutedbenzyl; C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl,C₁-C₆-halogenalkoxy or C₁-C₆-halogenalkylthio; C₁-C₈-alkyl-COR¹⁴;—CR¹⁵═N—O—R¹⁶, COR¹⁴; R¹⁰ represents H, halogen, cyano; substituted ornon substituted phenyl, substituted or non substituted benzyl,substituted or non substituted pyridyl; C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy orC₁-C₆-halogenalkylthio; C₁-C₈-alkyl-S(O)_(m)R¹¹; C₁-C₈-alkyl-SO₂NR¹²R¹³;C₁-C₈-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; mrepresents 0, 1 or 2; R¹¹ represents C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹²represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹³ represents H,C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹⁴ represents H, substituted or nonsubstituted, branched or linear C₁-C₈-alkyl, C₁-C₈-alkoxy; R¹⁵represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl; R¹⁶ represents H,C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₈-alkoxy, substituted or nonsubstituted benzyl; R¹² and R¹³ can form a 5- or 6-membered heterocycle,which can further comprise one or more heteroatoms selected in the groupconsisting of O, N, and S; R¹⁵ and R¹⁶ can form a heterocyclic 5- or6-membered ring, optionally including at least one further heteroatom;or a salt, an N-oxyde, a metallic complex, a metalloidic complex and/oran optically active or geometric isomer thereof.
 2. A phenyl-amidinederivative of formula (I) according to claim 1 wherein R¹ represents H,C₁-C₁₂-alkyl or SH; or R² represents methyl; or R³ representsC₂-C₁₂-alkyl, C₂-C₁₂-alkenyl; C₃-C₆-cycloalkyl; or R² and R³ can formtogether a substituted or non substituted 5- to 7-membered heterocycle;or R⁴ represents C₁-C₁₂-alkyl, a halogen atom or trifluoromethyl; or R⁵represents H, C₁-C₁₂-alkyl, a halogen atom or trifluoromethyl; or R⁷represents H, Cl, Br, I, nitro, cyano; phenyl; phenyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F, Cl, Br, I,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy;C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-halo-genalkyl,C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio; C₁-C₄-alkyl-S(O)_(m)R¹¹;C₁-C₄-alkyl-SO₂NR¹²R¹³; C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹,SO₂NR¹²R¹³, COR¹⁴; or R⁸ represents H, Cl, Br, I, cyano; phenyl; phenylsubstituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl-thio,C₁-C₄-halo-genalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio;C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; or R⁹ represents Cl, Br, I,cyano; phenyl substituted by F, Cl, Br, I, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl; benzyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogenalkylthio;C₁-C₄-alkyl-COR¹⁴; —CR¹⁵═N—O—R¹⁶, COR¹⁴; or R¹⁰ represents H, Cl, Br, I,cyano; phenyl; phenyl substituted by F, Cl, Br, I, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; benzyl;benzyl substituted by F, Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl,C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy; pyridyl; pyridyl substituted by F,Cl, Br, I, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₄-halogenoalkoxy; C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-halogenalkyl, C₁-C₄-halogenalkoxy or C₁-C₄-halogen-alkylthio;C₁-C₄-alkyl-S(O)_(m)R¹¹; C₁-C₄-alkyl-SO₂NR¹²R¹³; C₁-C₄-alkyl-COR¹⁴;—CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, COR¹⁴; or R¹⁵ represents H,C₁-C₆-alkyl, C₃-C₆-cycloalkyl; or R¹⁶ represents H, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, benzyl; benzyl substituted by halogen,C₁-C₄-alkyl or C₁-C₄-halogenoalkyl or a salt, an N-oxyde, a metalliccomplex, a metalloidic complex and/or an optically active or geometricisomer thereof.
 3. A phenyl-amidine derivative of formula (I) accordingto claim 1 wherein R¹ represents H or C₁-C₁₂-alkyl; or R³ represents anon substituted C₂-C₄-alkyl, C₃-C₄-alkenyl or cyclopropyl; or R² and R³can form together a 6-membered heterocycle; or R⁴ represents a nonsubstituted C₁-C₁₂-alkyl, a fluorine or a chlorine atom; or R⁵represents a non substituted C₁-C₁₂-alkyl, a fluorine or a chlorine atomor a salt, an N-oxyde, a metallic complex, a metalloidic complex and/oran optically active or geometric isomer thereof.
 4. A phenyl-amidinederivative of formula (I) according to claim 1 wherein R¹ represents Hor methyl; or R³ represents ethyl, n-propyl, i-propyl, propenyl orallyl; or R² and R³ can form together a pipiridinyl or a pyrolidinyl; orR⁴ represents methyl and ethyl; or R⁵ represents methyl or ethyl or asalt, an N-oxyde, a metallic complex, a metalloidic complex and/or anoptically active or geometric isomer thereof.
 5. A phenyl-amidinederivative of formula (I)

wherein R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl,a substituted or non substituted C₂-C₁₂-alkenyl, a substituted or nonsubstituted C₂-C₁₂-alkynyl, SH, or a substituted or non substitutedS—C₁-C₁₂-alkyl; R² and R³ form together a 2-alkylated-pyrolidinyl; R⁴represents a substituted or non substituted C₁-C₁₂-alkyl, a halogenatom, halogeno-C₁-C₁₂-alkyl, substituted or non substitutedO—C₁-C₁₂-alkyl, or cyano; R⁵ represents H, a substituted or nonsubstituted C₁-C₁₂-alkyl, a halogen atom, halogeno-C₁-C₁₂-alkyl,substituted or non substituted O—C₁-C₁₂-alkyl, or cyano; R⁶ represents aheterocycle selected from the group consisting of

R⁷ represents H, halogen, nitro, cyano, substituted or non substitutedphenyl, substituted or non substituted benzyl, C₁-C₈-alkyl,C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl,C₁-C₆-halogen-alkoxy, C₁-C₆-halogenalkylthio, C₁-C₈-alkyl-S(O)_(m)R¹¹,C₁-C₈-alkyl-SO₂NR¹²R¹³, C₁-C₈-alkyl-COR¹⁴, —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹,SO₂NR¹²R¹³, or COR¹⁴; R⁸ represents H, halogen, cyano, substituted ornon substituted phenyl, substituted or non substituted benzyl,C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl,C₁-C₆-halogenalkoxy, C₁-C₆-halogenalkylthio, C₁-C₈-alkyl-COR¹⁴,—CR¹⁵═N—O—R¹⁶, or COR¹⁴; R⁷ and R⁸ can form a carbocycle, which can besaturated, unsaturated or aromatic and substituted or non substituted byhalogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, or C₁-C₄-alkoxyalkyl; R⁹represents H, halogen, cyano, substituted phenyl, substituted or nonsubstituted benzyl, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio,C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy, C₁-C₆-halogenalkylthio,C₁-C₈-alkyl-COR¹⁴, —CR¹⁵═N—O—R¹⁶, or COR¹⁴; R¹⁰ represents H, halogen,cyano, substituted or non substituted phenyl, substituted or nonsubstituted benzyl, substituted or non substituted pyridyl, C₁-C₈-alkyl,C₁-C₈-alkoxy, C₁-C₈-alkylthio, C₁-C₆-halogenalkyl, C₁-C₆-halogenalkoxy,C₁-C₆-halogenalkylthio, C₁-C₈-alkyl-S(O)_(m)R¹¹, C₁-C₈-alkyl-SO₂NR¹²R¹³,C₁-C₈-alkyl-COR¹⁴, —CR¹⁵═N—O—R¹⁶, S(O)_(m)R¹¹, SO₂NR¹²R¹³, or COR¹⁴; mrepresents 0, 1, or 2; R¹¹ represents C₁-C₈-alkyl or C₃-C₆-cycloalkyl;R¹² represents H, C₁-C₈-alkyl or C₃-C₆-cycloalkyl; R¹³ represents H,C₁-C₈-alkyl or C₃-C₆-cycloalkyl; R¹⁴ represents H, substituted or nonsubstituted, branched or linear C₁-C₈-alkyl, or C₁-C₈-alkoxy; R¹⁵represents H, C₁-C₈-alkyl or C₃-C₆-cycloalkyl; R¹⁶ represents H,C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₈-alkoxy, or substituted or nonsubstituted benzyl; R¹² and R¹³ can form a 5- or 6-membered heterocycle,which can further comprise one or more heteroatoms selected in the groupconsisting of O, N, and S; R¹⁵ and R¹⁶ can form a heterocyclic 5- or6-membered ring, optionally including at least one further heteroatom;or a salt, an N-oxyde, a metallic complex, a metalloidic complex and/oran optically active or geometric isomer thereof.
 6. A phenyl-amidinederivative of formula (I) according to claim 5 wherein R² and R³ formtogether a 2-methyl-pyrolidinyl or a salt, an N-oxyde, a metalliccomplex, a metalloidic complex and/or an optically active or geometricisomer thereof.
 7. A phenyl-amidine derivative of formula (I) accordingto claim 1, wherein R¹ represents hydrogen; R² represents methyl; R³represents ethyl, n-propyl, i-propyl, propenyl or allyl; R⁴ representsmethyl or ethyl; and R⁵ represents methyl or ethyl or a salt, anN-oxyde, a metallic complex, a metalloidic complex and/or an opticallyactive or geometric isomer thereof.
 8. A phenyl-amidine derivative offormula (I) according to claim 1, wherein R¹ represents hydrogen; R²represents methyl; R³ represents ethyl; R⁴ represents methyl; and R⁵represents methyl or a salt, an N-oxyde, a metallic complex, ametalloidic complex and/or an optically active or geometric isomerthereof.
 9. A phenyl-amidine derivative of formula (I) according toclaim 1, wherein R¹ represents hydrogen; R² represents methyl; R³represents ethyl; R⁴ represents methyl; R⁵ represents methyl; and R⁶represents the following:

wherein R⁹ represents phenyl substituted by F, Cl, Br, I,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy or a salt, anN-oxyde, a metallic complex, a metalloidic complex and/or an opticallyactive or geometric isomer thereof.
 10. A phenyl-amidine derivative offormula (I) according to claim 9, wherein R⁹ represents phenylsubstituted by F, Cl, Br, or I or a salt, an N-oxyde, a metalliccomplex, a metalloidic complex and/or an optically active or geometricisomer thereof.
 11. A phenyl-amidine derivative of formula (I) accordingto claim 10, wherein R⁹ represents phenyl substituted by Cl or Br or asalt, an N-oxyde, a metallic complex, a metalloidic complex and/or anoptically active or geometric isomer thereof.
 12. A phenyl-amidinederivative of formula (I) according to claim 1, wherein R¹ representshydrogen; R² represents methyl; R³ represents i-Pr; R⁴ representsmethyl; R⁵ represents methyl; and R⁶ represents the following:

wherein R¹⁰ represents CF₃ or a salt, an N-oxyde, a metallic complex, ametalloidic complex and/or an optically active or geometric isomerthereof.
 13. A phenyl-amidine derivative of formula (I) according toclaim 5, wherein R¹ represents hydrogen; R⁴ represents methyl; and R⁵represents methyl; or a salt, an N-oxyde, a metallic complex, ametalloidic complex and/or an optically active or geometric isomerthereof.
 14. A phenyl-amidine derivative of formula (I) according toclaim 1, wherein R¹ represents hydrogen; R² represents methyl; R³represents ethyl, propyl, i-Pr, n-Pr, or butyl; R⁴ represents methyl; R⁵represents H or methyl; and R⁶ represents the following:


15. A phenyl-amidine derivative of formula (I):

wherein R¹ represents H, a substituted or non substituted C₁-C₁₂-alkyl,a substituted or non substituted C₂-C₁₂-alkenyl, a substituted or nonsubstituted C₂-C₁₂-alkynyl, SH, or a substituted or non substitutedS—C₁-C₁₂-alkyl; R² represents methyl; R³ represents a substituted or nonsubstituted C₂-C₁₂-alkyl, substituted or non substitutedC₃-C₆-cycloalkyl, substituted or non substituted C₂-C₁₂-alkenyl,substituted or non substituted C₂-C₁₂-alkynyl, halogeno-C₁-C₁₂-alkyl; orR¹ and R², R¹ and R³, or R² and R³ can form together a substituted ornon substituted 5- to 7-membered heterocycle; R⁴ represents asubstituted or non substituted C₁-C₁₂-alkyl, a halogen atom,halogeno-C₁-C₁₂-alkyl, substituted or non substituted 0-C₁-C₁₂-alkyl, orcyano; R⁵ represents H, a substituted or non substituted C₁-C₁₂-alkyl, ahalogen atom, halogeno-C₁-C₁₂-alkyl, substituted or non substitutedO—C₁-C₁₂-alkyl, or cyano; R⁶ represents the following:

wherein R⁹ represents H, halogen, cyano, phenyl substituted by F, Cl,Br, I, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy;substituted or non substituted benzyl, C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylthio, C₁-C₆-halo-genalkyl, C₁-C₆-halogenalkoxy,C₁-C₆-halogenalkylthio, C₁-C₈-alkyl-COR¹⁴, —CR¹⁵═N—O—R¹⁶, or COR¹⁴; R¹⁴represents H, substituted or non substituted, branched or linearC₁-C₈-alkyl, C₁-C₈-alkoxy; R¹⁵ represents H, C₁-C₈-alkyl orC₃-C₆-cycloalkyl; R¹⁶ represents H, C₁-C₈-alkyl, C₃-C₆-cycloalkyl,C₁-C₈-alkoxy, or substituted or non substituted benzyl; and R¹⁵ and R¹⁶can form a heterocyclic 5- or 6-membered ring, optionally including atleast one further heteroatom; or a salt, an N-oxyde, a metallic complex,a metalloidic complex and/or an optically active or geometric isomerthereof.
 16. A phenyl-amidine derivative of formula (I) according toclaim 15, wherein R¹ represents hydrogen; R² represents methyl; R³represents methyl, ethyl, propyl, i-Pr, n-Pr, or butyl; R⁴ representsmethyl; R⁵ represents methyl; and R⁹ represents a phenyl substituted byF, Cl, Br, or I; or a salt, an N-oxyde, a metallic complex, ametalloidic complex and/or an optically active or geometric isomerthereof.
 17. A phenyl-amidine derivative of formula (I) according toclaim 16, wherein R⁹ is phenyl substituted by chlorine or bromine; or asalt, an N-oxyde, a metallic complex, a metalloidic complex and/or anoptically active or geometric isomer thereof.
 18. A method forcontrolling phytopathogenic fungi of crops, comprising applying anagronomically effective and substantially non-phytotoxic quantity of aphenyl-amidine derivative or a salt, an N-oxyde, a metallic complex, ametalloidic complex and/or an optically active or geometric isomerthereof according to claim 1 to soil where a plant is growing or iscapable of growing, to leaves and/or to fruit of a plant or to seeds ofa plant.
 19. A method for controlling damaging insects comprisingapplying a phenyl-amidine derivative of formula (I) or a salt, anN-oxyde, a metallic complex, a metalloidic complex and/or an opticallyactive or geometric isomer thereof according to claim 1 to seed, a plantand/or to fruit of a plant or to soil wherein a plant is growing orwherein said plant is desired to grow.